(3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate

Base Information

• Chemical Name: (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate
• CAS No.: 1347742-64-6
• Molecular Formula: C₂₉H₄₀O₁₀
• Molecular Weight: 548.631
• Mol file: 1347742-64-6.mol

Synonyms:(3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate

Chemical Property of (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate

There total 11 articles about (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

(3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane (1346752-72-4) + acetic anhydride (108-24-7) → (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate (1347742-64-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate (1347742-64-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: benzene / 4 h / Reflux; Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux

3.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.08 h / -78 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

7.2: 4 h / -78 - 20 °C

8.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 2 h / 0 - 20 °C / Inert atmosphere

9.1: hydrogen; palladium(II) hydroxide / benzene / 5 h / 20 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

11.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 3 h / -40 °C / Inert atmosphere

12.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; titanium tetrachloride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene; 1.1: Wittig reaction / 4.2: Crimmins aldol reaction;

DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

C31H46O8Si → (3S,5S)-1,7-bis(3,4,5-trimethoxyphenyl)heptane-3,5-diyl diacetate (1347742-64-6)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 2 h / 0 - 20 °C / Inert atmosphere

2: hydrogen; palladium(II) hydroxide / benzene / 5 h / 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

4: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 3 h / -40 °C / Inert atmosphere

5: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; acetic acid; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;

DOI:10.1016/j.tetasy.2011.11.010

upstream raw materials:

(3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane

acetic anhydride

(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-(3,4,5-trimethoxyphenyl)pentan-1-one

(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

Downstream raw materials:

(3S,5S)-3,5-dihydroxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane

Refernces